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Kathie Lee Gifford opens up about what she really thinks of liberal Hollywood, her fears for America… and her unforgettable encounter with Frank Sinatra at Reagan’s inauguration

by LJ News Opinions
June 27, 2026
in Entertainment
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If any one person has been the most surprised by the scope and longevity of Kathie Lee Gifford‘s celebrated, decades-long entertainment career, it may be her.

‘I’ve always felt like Waldo,’ Gifford, 72, tells the Daily Mail in an exclusive interview, comparing herself to the titular children’s book character, an unwitting eyewitness to history’s great events.

Such was the case when Gifford performed at President Ronald Reagan’s second inauguration in 1985. ‘It’s like, why in the world is this skinny little kid from Bowie, Maryland singing for the president?’ she remembered, laughing.

Giffords comes off as both humble and irrepressibly optimistic.

‘They needed somebody quickly and I was available, so I just went,’ she says, ‘Those were the good old days, when we didn’t think about if we’re a Republican or a Democrat, we’re just American.’

‘Like a lot of things in my life, it was a fluke.’

If any one person has been the most surprised by the scope and longevity of Kathie Lee Gifford’s celebrated, decades-long entertainment career, it may be her

Gifford performed at President Ronald Reagan's second inauguration. 'It's like, why in the world is this skinny little kid from Bowie, Maryland singing for the president?' she remembered

Gifford performed at President Ronald Reagan’s second inauguration. ‘It’s like, why in the world is this skinny little kid from Bowie, Maryland singing for the president?’ she remembered

Perhaps, but as Gifford’s career – as a cost-host of Live! with Regis and Kathie Lee for 15 years and later as a Today Show co-host – suggests, talent may have had something to do with it.

‘Frank Sinatra was standing next to my manager,’ Gifford says of that inauguration day at the US Capitol Building, ‘and I was rehearsing and Sinatra said, “the kid can sing.”

‘I’ve thought about that every time I’ve gotten a bad review, which has been often,’ she joked.

The irony is not lost on Gifford that four decades later, she’d be asked to write and perform a song for the soundtrack of a biopic about President Ronald Reagan and his wife Nancy.

The movie, Reagan, starring Dennis Quaid and Penelope Ann Miller, will be re-released in more than a dozen cities on July 4, marking the 250th anniversary of America’s founding.

Gifford was drawn to the project, she says, as much by the performance of Quaid, as by the story of the Reagan’s marriage. Her positivity dims, for only a moment, as she laments that Quaid did not get the recognition he deserved from Hollywood.

‘Dennis Quaid’s performance, I thought, was Oscar-worthy,’ Gifford tells the Daily Mail. ‘I truly did. I said, there’s a possibility he can get nominated for this performance and then I thought to myself, no, it’s Reagan, so they won’t even give it a fair shot. It’s just the world we live in. It’s unfair, and it’s sad to me.’

But the politics, she insists, aren’t as important as the bigger picture.

As Gifford's career – as a cost-host of Live! with Regis and Kathie Lee for 15 years and later as a Today Show co-host – suggests, talent may have had something to do with it

As Gifford’s career – as a cost-host of Live! with Regis and Kathie Lee for 15 years and later as a Today Show co-host – suggests, talent may have had something to do with it

The movie, Reagan , starring Dennis Quaid (left as Ronald Reagan) and Penelope Ann Miller (right as Nancy Reagan), will be re-released in more than a dozen cities on July 4

The movie, Reagan , starring Dennis Quaid (left as Ronald Reagan) and Penelope Ann Miller (right as Nancy Reagan), will be re-released in more than a dozen cities on July 4

‘This is a love story. Yes, there’s politics involved. Yes, there’s history being made. But at its core, it’s a love story.’

Songwriter Richard Spitz and Gifford wrote the duet ‘I Knew It Would Be You,’ which she then recorded with country singer Josh Turner.

‘You couldn’t be around [the Reagans] without realizing how deeply they loved each other,’ Gifford says of the first couple. ‘It was palpable. It was obvious. They just adored each other.’

Gifford’s appreciation for Reagan is a personal one. Her late husband Frank Gifford, the NFL star and sports commentator, was a friend of the president.

‘Frank adored Ronnie, everybody adored Ronnie,’ she says, insisting that the president did not seem, to her, to be a particularly partisan figure. ‘Ronnie started out as a Democrat. People forget that. He was president of the Screen Actor’s Guild (SAG) Union. This was a moderate, literate and good man.’

‘One of my favorite pictures is in my library in Connecticut, and it’s, me standing next to Bob Hope on one side of me, President Reagan on the other, and then Mrs. Reagan, just the four of us,’ Gifford says.

‘I must have been, like, in my early, early 20s,’ she says. ‘It’s like so many of the pictures in my career, I just go, what’s Waldo doing there?’

Gifford has similar feelings about the time she found herself at actor Kevin Costner’s house seated next to President of the Soviet Union Mikhail Gorbachev. 

‘[Gorbachev] was a lovely man. Of course, his translator, that we all knew from seeing him on the news, was there. He was stuck with me for two hours at dinner. I’ll never forget it.’

So many years later, Gifford concedes that the America may feel like a different place, but her hope for its future – rooted in her deep faith and spiritually – is evident.

'Frank adored Ronnie, everybody adored Ronnie,' Gifford says (Pictured: President Reagan talking with Christopher Reeve and Frank Gifford at the White House in 1983)

‘Frank adored Ronnie, everybody adored Ronnie,’ Gifford says (Pictured: President Reagan talking with Christopher Reeve and Frank Gifford at the White House in 1983)

'One of my favorite pictures is in my library in Connecticut, and it's, me standing next to Bob Hope on one side of me, President Reagan on the other, and then Mrs. Reagan, just the four of us,' Gifford says

‘One of my favorite pictures is in my library in Connecticut, and it’s, me standing next to Bob Hope on one side of me, President Reagan on the other, and then Mrs. Reagan, just the four of us,’ Gifford says

‘I think the world is full of either people that are fearful, or people that are fearless. And I’ve always been more of a fearless person. Am I concerned about certain things? Yeah,’ she says.

What those ‘things’ are, Gifford – a true professional – is discreet, abiding by the advice that another great communicator gave her early on in her career.

‘I met Reverend Billy Graham in my early 20s and he became one of my dearest friends for the rest of his life.

‘He said, the only thing I really regret that I did in my life that I would like to have back is when I got involved with politics, because the minute you open your mouth, you lose half your audience.

‘I’ll take someone’s kindness any day over their opinion,’ says Gifford, who also does not shy away from expressing her appreciation for her country.

‘I love our Constitution, and I believe that that grants us the right to think the way we want to, worship the way we want to, and vote the way we want to. And then we deserve the government we vote for. That’s our cherished, cherished heritage.’

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